Early work

Littlefield's first entry into politics was with the Maine Senate Republican Caucus, where he worked to elect Republicans to the Maine Senate. That position led to an opportunity to join Governor John McKernan's successful re-election campaign in 1990.^[6] There, he served as a field director, tasked with winning three communities with Republican registration deficits of 2-1.

Littlefield then served on the staff of Maine congressman Jim Longley, Jr. in Washington. The following year he directed Longley’s re-election campaign ground efforts.

After serving Longley, Littlefield moved on to work as Political Director for the National Federation of Independent Business.^[7] There he was involved in a number of political efforts including the small business group's IRS reform effort.

Prior to founding Littlefield Consulting, he served as a Partner in the Washington, DC based Republican political consulting firm Political Solutions, which he founded in 2000.^[8] There, Littlefield worked for Presidential candidate Fred Thompson,^[9] U.S. Senators, Members of the United States Congress, including Congresswoman Shelley Moore Capito,^[10] and others.

Littlefield Consulting

Littlefield founded a new political consulting firm, Littlefield Consulting, LLC in April 2008, with the stated goal of focusing on "advising GOP candidates and free-market-advocacy organizations."^[11]

Since its founding, Littlefield has worked with the Republican National Committee,^[12] as well as a number of Republican 527 groups.

Senior political advisor to Governor LePage

In January 2010, Littlefield was brought on as senior political advisor to then Mayor Paul LePage, of Waterville, Maine.^[13]

Once on board, he was credited with orchestrating the political strategy responsible for LePage winning a seven-way contested primary, and being the first Republican in sixteen years to win a gubernatorial election in the fall.

The strategy was highly dependent on Littlefield having persuaded LePage to talk about his life story of overcoming adversity, which became major campaign themes. John Morris, LePage's campaign chief of staff, credits Littlefield for sharpening the campaign's focus and coming up with what he referred to as the "three onlys" theme before the Republican primary in June. "Paul was the only candidate who had a compelling life story. Paul was the only candidate who had a successful experience as a chief executive officer of a government entity. And Paul was the only candidate who was the executive of a prosperous Maine business," Morris said.

On November 2, 2010, Paul LePage won a narrow three-way race by roughly 10,000 votes. Since that time, Littlefield has continued to serve as senior political advisor for the LePage administration.

Media pundit

In addition to his work as a political consultant, Littlefield is frequently an on-air contributor for MSNBC and other media outlets, where he comments on current events from a conservative perspective, and provides insights from a campaign professional.^[14]